ethyl N-methylaminooxyacetate | 5767-05-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl N-methylaminooxyacetate
• 英文别名: N-Methyl-aminooxy-essigsaeure-aethylester；Ethyl 2-(methylaminooxy)acetate
• CAS: 5767-05-5
• 化学式: C₅H₁₁NO₃
• 分子量: 133.147
• InChiKey: LDQQDLADOKXFTM-UHFFFAOYSA-N

物化性质

• 沸点：
  82 °C
• 密度：
  1.026±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl N-methylaminooxyacetate 在 氢氧化钾 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 N-methylaminooxyacetic acid
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Thio-Containing Compounds with Serum HDL-Cholesterol-Elevating Properties

  摘要：

  A novel series of substituted sulfanyldihydroimidazolones (1) that modulates high-density lipoprotein cholesterol (HDL-C) has been reported to have HDL-elevating properties in several animal models. Concerns about the chemical and metabolic stability of I directed us to explore the structure-activity relationship (SAR) of a related series of substituted thiohydantoins (2). Expansion of the scope of the thiohydantoin series led to exploration of compounds in related thio-containing ring systems 3-7 and the N-cyanoguanidine derivative 8. Compounds were tested sequentially in three animal models to assess their HDL-C elevating efficacy and safety profiles. Further evaluation of selected compounds in a dose-response paradigm culminated in the identification of compound 2.39 as a candidate compound for advanced preclinical. studies.

  DOI：

  10.1021/jm030219z
• 作为产物：
  描述：

  Ethyl 2-(methylideneamino)oxyacetate 在 盐酸 、 sodium cyanoborohydride 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以58%的产率得到ethyl N-methylaminooxyacetate
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Thio-Containing Compounds with Serum HDL-Cholesterol-Elevating Properties

  摘要：

  A novel series of substituted sulfanyldihydroimidazolones (1) that modulates high-density lipoprotein cholesterol (HDL-C) has been reported to have HDL-elevating properties in several animal models. Concerns about the chemical and metabolic stability of I directed us to explore the structure-activity relationship (SAR) of a related series of substituted thiohydantoins (2). Expansion of the scope of the thiohydantoin series led to exploration of compounds in related thio-containing ring systems 3-7 and the N-cyanoguanidine derivative 8. Compounds were tested sequentially in three animal models to assess their HDL-C elevating efficacy and safety profiles. Further evaluation of selected compounds in a dose-response paradigm culminated in the identification of compound 2.39 as a candidate compound for advanced preclinical. studies.

  DOI：

  10.1021/jm030219z

文献信息

• Amino thioxomethyl amino oxyacetic acid derivatives
  申请人：American Home Products Corporation

  公开号：US20020045776A1

  公开（公告）日：2002-04-18

  Antiatherosclerotic compounds are provided which have the following structure: 1 wherein R is lower alkyl; R 1 is hydroxy, amino, or lower alkoxy, R 2 and R 3 are each independently hydrogen, alkyl or aryl; Ar is phenyl, indanyl, benzhydryl, or phenyl substituted with one or more member selected from the group consisting of halogen, lower alkyl, perfluoroalkyl, lower alkoxy, perfluoroalkylalkoxy, dialkylamino, and aryloxy; or pharmaceutically acceptable salts thereof.

  提供了具有以下结构的抗动脉粥样硬化化合物：其中R是较低的烷基；R1是羟基、氨基或较低的烷氧基；R2和R3各自独立地是氢、烷基或芳基；Ar是苯基、茚基、苯甲基或苯基，其中一个或多个成员被选自卤素、较低的烷基、全氟烷基、较低的烷氧基、全氟烷氧基、二烷基氨基和芳氧基组成的群体所取代；或其药用盐。
• Kornowski,H. et al., Bulletin de la Societe Chimique de France, 1966, p. 683 - 686
  作者：Kornowski,H. et al.

  DOI：——

  日期：——
• Design, Synthesis, and Biological Evaluation of Thio-Containing Compounds with Serum HDL-Cholesterol-Elevating Properties
  作者：Hassan Elokdah、Theodore S. Sulkowski、Magid Abou-Gharbia、John A. Butera、Sie-Yearl Chai、Geraldine R. McFarlane、Mar-Lee McKean、John L. Babiak、Steven J. Adelman、Elaine M. Quinet

  DOI：10.1021/jm030219z

  日期：2004.1.1

  A novel series of substituted sulfanyldihydroimidazolones (1) that modulates high-density lipoprotein cholesterol (HDL-C) has been reported to have HDL-elevating properties in several animal models. Concerns about the chemical and metabolic stability of I directed us to explore the structure-activity relationship (SAR) of a related series of substituted thiohydantoins (2). Expansion of the scope of the thiohydantoin series led to exploration of compounds in related thio-containing ring systems 3-7 and the N-cyanoguanidine derivative 8. Compounds were tested sequentially in three animal models to assess their HDL-C elevating efficacy and safety profiles. Further evaluation of selected compounds in a dose-response paradigm culminated in the identification of compound 2.39 as a candidate compound for advanced preclinical. studies.